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Ligand (S)-scoulerine

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Biosynthesis of alkaloids derived from shikimate pathway, Biosynthesis of secondary metabolites, Isoquinoline alkaloid biosynthesis

MetaCyc

berberine biosynthesis, chelerythrine biosynthesis, coptisine biosynthesis, dehydroscoulerine biosynthesis, epiberberine biosynthesis, noscapine biosynthesis, palmatine biosynthesis, sanguinarine and macarpine biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Natural Substrate (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.65

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-cheilanthifoline + [oxidized NADPH-hemoprotein reductase] + 2 H2O

746047

-

1.14.19.65

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-cheilanthifoline + [oxidized NADPH-hemoprotein reductase] + H2O

700725, 728446, 395597

-

1.14.19.65

2 entries

1.14.19.73

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

673579

-

1.5.3.12

(S)-scoulerine + O2 = ?

725505

-

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = ?

15195, 15192, 15194, 15196

6neh, 3D-view

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = ?

15195, 15192, 15194, 15196

6nej, 3D-view

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine

727532, 733669

6neh, 3D-view

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine

727532, 733669

6nej, 3D-view

2.1.1.117

4 entries

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.3

(S)-reticuline + O2 = (S)-scoulerine + H2O2

0

3fw9, 3D-view

Substrate in Enzyme-catalyzed Reactions (18 results)

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Show Substrate (18 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.11.32

(S)-scoulerine + 2-oxoglutarate + O2 = ?

725537

-

1.14.19.64

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

673579

-

1.14.19.64

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = ?

673579

-

1.14.19.64

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = nandinine + [oxidized NADPH-hemoprotein reductase] + 2 H2O

746047

-

1.14.19.65

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-cheilanthifoline + [oxidized NADPH-hemoprotein reductase] + 2 H2O

746047

-

1.14.19.65

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-cheilanthifoline + [oxidized NADPH-hemoprotein reductase] + H2O

700725, 728446, 711025, 395597

-

1.14.19.65

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

711025

-

1.14.19.64

3 entries

1.14.19.65

3 entries

1.14.19.73

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

673579

-

1.21.3.3

(S)-scoulerine + H2O2 = (S)-reticuline + O2

727000

3fw9, 3D-view

1.5.3.12

(S)-scoulerine + O2 = ?

725505

-

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = ?

15195, 15192, 15194, 15196

6neh, 3D-view

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = ?

15195, 15192, 15194, 15196

6nej, 3D-view

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine

727532, 15195, 15196, 15192, 15193, 15194, 720655, 733669, 756838, 756272

6neh, 3D-view

2.1.1.117

S-Adenosyl-L-methionine + (S)-scoulerine = S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine

727532, 15195, 15196, 15192, 15193, 15194, 720655, 733669, 756838, 756272

6nej, 3D-view

2.1.1.117

S-adenosyl-L-methionine + (S)-scoulerine = S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine + 2-O-methylscoulerine + tetrahydropalmatine

757982

6neh, 3D-view

2.1.1.117

S-adenosyl-L-methionine + (S)-scoulerine = S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine + 2-O-methylscoulerine + tetrahydropalmatine

757982

6nej, 3D-view

2.1.1.117

6 entries

2.1.1.128

S-Adenosyl-L-methionine + (S)-scoulerine = S-Adenosyl-L-homocysteine + jatrorrhizine

15229

-

2.1.1.300

S-adenosyl-L-methionine + (S)-scoulerine = S-adenosyl-L-homocysteine + N-methyl-(S)-scoulerine

723837

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.3

(S)-reticuline + O2 = (S)-scoulerine + H2O2

0

3fw9, 3D-view

1.21.3.3

reticuline + O2 = (S)-scoulerine + (S)-coreximine + H2O2

0

3fw9, 3D-view

1.21.3.3

2 entries

2.1.1.115

S-Adenosylmethionine + (S)-norreticuline = S-Adenosylhomocysteine + (S)-scoulerine

15190

-

Inhibitor in Enzyme-catalyzed Reactions (4 results)

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Show Inhibitors (4 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.3

-

393873

3fw9, 3D-view

1.21.3.3

50% inhibition at 0.01 mM

393870

3fw9, 3D-view

1.21.3.3

2 entries

3.4.23.46

24.34% inhibition at 0.005 mM

753620

-

5.6.2.1

inhibition comparable to camptothecin

691728

-

3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (5 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.21.3.3

3fw9, 3D-view

2.1.1.117

6neh, 3D-view

2.1.1.117

6nej, 3D-view

2.1.1.117

6neh, 3D-view

2.1.1.117

6nej, 3D-view

2.1.1.117

4 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.21.3.3

0.0025

-

-

700673

2.1.1.117

0.01

-

product 2-O-methylscoulerine, pH 8.4, 35°C

757982

2.1.1.117

0.02

-

product (S)-tetrahydrocolumbamine, pH 8.4, 35°C

757982

2.1.1.117

2 entries

K_M Value (12 results)

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Show KM Value (12 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.19.64

0.00054

-

CYP719A3 variant, determined with HPLC

673579

1.14.19.65

0.0009

-

-

395597

1.14.19.65

1.9

-

pH 8.0, 30°C, kcat: 100%

711025

1.14.19.65

8.1

-

pH 8.0, 30°C, kcat: 29%

711025

1.14.19.65

3 entries

1.14.19.73

0.00054

-

microsomal protein, pH 7.6, 30°C

673579

1.21.3.3

0.035

-

-

700673

1.5.3.12

0.146

-

pH 8.8, 37°C

725505

2.1.1.117

0.0219

-

product 2-O-methylscoulerine, pH 8.4, 35°C

757982

2.1.1.117

0.0245

-

product (S)-tetrahydrocolumbamine, pH 8.4, 35°C

757982

2.1.1.117

0.0536

-

pH 9, 37°C

756272

2.1.1.117

0.1

-

-

15193

2.1.1.117

1.6

-

-

15196

2.1.1.117

5 entries

References & Links

Literature References (28)

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Show Reference (28 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

15190

-

Purification and characterization of three isoforms of S-adenosyl-L-methionine: (R,S)-tetrahydrobenzylisoquinoline-N-methyltransferase from Berberis koetineana cell cultures

1990

Frenzel, T.; Zenk, M.H.

Phytochemistry

29

3491-3497

15192

-

Expression of (S)-scoulerine 9-O-methyltransferase in Coptis japonica plants

1993

Fujiwara, H.; Takeshita, N.; Terano, Y.; Fitchen, J.H.; Tsujita, T.; Katagiri, Y.; Sato, F.; Yamada, Y.

Phytochemistry

34

949-954

15193

-

S-Adenosyl-L-methionine:scoulerine-9-O-methyltransferase from cultured Coptis japonica cells

1993

Sato, F.; Takeshita, N.; Fitchen, J.H.; Fujiwara, H.; Yamada, Y.

Phytochemistry

32

659-664

15194

7719631

Molecular cloning and characterization of S-adenosyl-L-methionine:scoulerine 9-O-methyltransferase from cultured cells of Coptis japonica

1995

Takeshita, N.; Fujiwara, H.; Mimura, H.; Fitchen, J.H.; Yamada, Y.; Sato, F.

Plant Cell Physiol.

36

29-36

15195

24241402

Alternative final steps in berberine biosynthesis in Coptis japonica cell cultures

1988

Galneder, E.; Rueffer, M.; Wanner, G.; Tabata, M.; Zenk, M.H.

Plant Cell Rep.

7

1-4

15196

24253642

S-Adenosyl-L-methionine:(S)-scoulerine 9-O-methyltransferase, a highly stereo- and regio-specific enzyme in tetrahydroprotoberberine biosynthesis

1985

Muemmler, S.; Rueffer, M.; Nagakura, N.; Zenk, M.H.

Plant Cell Rep.

4

36-39

15229

17405035

Partial purification and properties of S-adenosylmethionine:(R),(S)-norlaudanosoline-6-O-methyltransferase from Argemone platyceras cell culture

1983

Rueffer, M.; Nagakura, N.; Zenk, M.H.

J. Med. Plant Res.

49

131-137

393870

7592663

Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants

1995

Kutchan, T.M.; Dittrich, H.

J. Biol. Chem.

270

24475-24481

393873

-

Purification and characterization of the berberine bridge enzyme from Berberis beaniana cell cultures

1985

Steffens, P.; Nagakura, N.; Zenk, M.H.

Phytochemistry

24

2577-2583

395597

-

Two methylenedioxy bridge forming cytochrome P-450 dependent enzymes are involved in (S)-stylopine biosynthesis

1991

Bauer, W.; Zenk, M.H.

Phytochemistry

30

2953-2961

673579

17250743

Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica

2007

Ikezawa, N.; Iwasa, K.; Sato, F.

FEBS J.

274

1019-1035

691728

18649321

DNA topoisomerase I inhibitory alkaloids from Corydalis saxicola

2008

Cheng, X.; Wang, D.; Jiang, L.; Yang, D.

Chem. Biodivers.

5

1335-1344

700673

19570558

Berberine bridge enzyme catalyzes the six electron oxidation of (S)-reticuline to dehydroscoulerine

2009

Winkler, A.; Puhl, M.; Weber, H.; Kutchan, T.M.; Gruber, K.; Macheroux, P.

Phytochemistry

70

1092-1097

700725

18854999

CYP719A subfamily of cytochrome P450 oxygenases and isoquinoline alkaloid biosynthesis in Eschscholzia californica

2009

Ikezawa, N.; Iwasa, K.; Sato, F.

Plant Cell Rep.

28

123-133

711025

21094631

Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana

2011

Diaz Chavez, M.L.; Rolf, M.; Gesell, A.; Kutchan, T.M.

Arch. Biochem. Biophys.

507

186-193

720655

20427510

Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica

2010

Takemura, T.; Ikezawa, N.; Iwasa, K.; Sato, F.

Plant Cell Physiol.

51

949-959

723837

18997344

Purification, crystallization and X-ray diffraction analysis of pavine N-methyltransferase from Thalictrum flavum

2008

Jain, A.; Ziegler, J.; Liscombe, D.K.; Facchini, P.J.; Tucker, P.A.; Panjikar, S.

Acta Crystallogr. Sect. F

64

1066-1069

725505

23118227

Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis

2012

Hagel, J.M.; Beaudoin, G.A.; Fossati, E.; Ekins, A.; Martin, V.J.; Facchini, P.J.

J. Biol. Chem.

287

42972-42983

725537

23928311

Dioxygenases catalyze O-demethylation and O,O-demethylenation with widespread roles in benzylisoquinoline alkaloid metabolism in opium poppy

2013

Farrow, S.C.; Facchini, P.J.

J. Biol. Chem.

288

28997-29012

727000

22931234

Isotope effects suggest a stepwise mechanism for berberine bridge enzyme

2012

Gaweska, H.M.; Roberts, K.M.; Fitzpatrick, P.F.

Biochemistry

51

7342-7347

727532

24316226

Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy

2014

Dang, T.T.; Facchini, P.J.

FEBS Lett.

588

198-204

728446

22421633

Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells

2013

Takemura, T.; Ikezawa, N.; Iwasa, K.; Sato, F.

Phytochemistry

91

100-108

733669

-

Homology modeling and molecular docking studies of (S)-scoulerine 9-O-methyltransferase from Coptis chinensis

2012

Zhu, Q.; Zhou, J.; Zhang, G.; Liao, H.

Chin. J. Chem.

30

2533-2538

746047

-

Cloning and characterization of Cheilanthifoline and stylopine synthase genes from Chelidonium majus

2017

Yahyazadeh, M.; Ratmoyo, P.; Bittner, F.; Sato, F.; Selmar, D.

Plant Cell Physiol.

58

1421-1430

753620

26779945

Application of BACE1 immobilized enzyme reactor for the characterization of multifunctional alkaloids from Corydalis cava (Fumariaceae) as Alzheimers disease targets

2016

Chlebek, J.; De Simone, A.; Hostalkova, A.; Opletal, L.; Perez, C.; Perez, D.I.; Havlikova, L.; Cahlikova, L.; Andrisano, V.

Fitoterapia

109

241-247

756272

31865477

Identification and characterization of methyltransferases involved in benzylisoquinoline alkaloids biosynthesis from Stephania intermedia

2019

Zhao, W.; Shen, C.; Zhu, J.; Ou, C.; Liu, M.; Dai, W.; Liu, X.; Liu, J.

Biotechnol. Lett.

42

461-469

756838

29915609

Identification and characterization of genes involved in benzylisoquinoline alkaloid biosynthesis in coptis species

2018

He, S.; Liang, Y.; Cong, K.; Chen, G.; Zhao, X.; Zhao, Q.; Zhang, J.; Wang, X.; Dong, Y.; Yang, J.; Zhang, G.; Qian, Z.; Fan, W.; Yang, S.

Front. Plant Sci.

9

731

757982

28922749

Unraveling additional O-methylation steps in benzylisoquinoline alkaloid biosynthesis in California poppy (Eschscholzia californica)

2017

Purwanto, R.; Hori, K.; Yamada, Y.; Sato, F.

Plant Cell Physiol.

58

1528-1540

Links to other databases for (S)-scoulerine

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Show Links (1 entry)

ChEBI

PubChem